# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1451655'
_audit_update_record             
;
2016-08-13 deposited with the CCDC.
2016-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'benzimidazolium salicylate'
_chemical_name_common            '[BIM+][SA-]'
_chemical_melting_point          397-401
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 N2 O3'
_chemical_formula_weight         256.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.3538(4)
_cell_length_b                   6.7000(4)
_cell_length_c                   24.9855(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.147(2)
_cell_angle_gamma                90.00
_cell_volume                     1226.08(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2558
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      28.36

_exptl_crystal_description       blocks
_exptl_crystal_colour            'light pink'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9631
_exptl_absorpt_correction_T_max  0.9775
_exptl_absorpt_process_details   'SADABS Bruker 2001'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker DUO APEX II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12298
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.78
_diffrn_reflns_theta_max         28.36
_reflns_number_total             3047
_reflns_number_gt                2558
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker DUO APEX II'
_computing_cell_refinement       Saint-Plus
_computing_data_reduction        Saint-Plus
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    X-Seed
_computing_publication_material  X-Seed

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0547P)²+0.2722P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3047
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1072
_refine_ls_wR_factor_gt          0.1006
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O8 O 0.02503(12) 0.97854(12) 0.08957(3) 0.0308(2) Uani 1 1 d . . .
O9 O -0.15543(14) 0.73888(13) 0.11727(4) 0.0357(2) Uani 1 1 d . . .
O10 O -0.35997(13) 0.80643(14) 0.19241(4) 0.0374(2) Uani 1 1 d . . .
H10 H -0.3172 0.7415 0.1677 0.045 Uiso 1 1 calc R . .
N11 N 0.18519(13) 0.71639(14) 0.03161(4) 0.0244(2) Uani 1 1 d . . .
H11 H 0.133(2) 0.825(3) 0.0515(7) 0.054(5) Uiso 1 1 d . . .
N18 N 0.20632(13) 0.49392(14) -0.03166(4) 0.0241(2) Uani 1 1 d . . .
H18 H 0.183(2) 0.426(3) -0.0657(7) 0.050(5) Uiso 1 1 d . . .
C1 C -0.13959(14) 1.04423(16) 0.16492(4) 0.0207(2) Uani 1 1 d . . .
C6 C -0.27412(15) 0.98463(17) 0.19817(4) 0.0234(2) Uani 1 1 d . . .
C7 C -0.08522(15) 0.91211(16) 0.12096(4) 0.0229(2) Uani 1 1 d . . .
C2 C -0.05731(15) 1.23091(17) 0.17360(5) 0.0252(2) Uani 1 1 d . . .
H2 H 0.0340 1.2724 0.1514 0.030 Uiso 1 1 calc R . .
C4 C -0.24062(17) 1.29514(19) 0.24623(5) 0.0293(3) Uani 1 1 d . . .
H4 H -0.2751 1.3808 0.2739 0.035 Uiso 1 1 calc R . .
C17 C 0.29237(14) 0.41295(17) 0.01505(4) 0.0227(2) Uani 1 1 d . . .
C19 C 0.14343(15) 0.67329(17) -0.02000(5) 0.0250(2) Uani 1 1 d . . .
H19 H 0.0776 0.7590 -0.0451 0.030 Uiso 1 1 calc R . .
C5 C -0.32415(16) 1.11194(19) 0.23866(4) 0.0277(3) Uani 1 1 d . . .
H5 H -0.4157 1.0722 0.2610 0.033 Uiso 1 1 calc R . .
C3 C -0.10631(16) 1.35645(18) 0.21390(5) 0.0288(3) Uani 1 1 d . . .
H3 H -0.0491 1.4828 0.2194 0.035 Uiso 1 1 calc R . .
C12 C 0.27889(14) 0.55504(17) 0.05540(4) 0.0235(2) Uani 1 1 d . . .
C16 C 0.37495(16) 0.22843(18) 0.02553(5) 0.0301(3) Uani 1 1 d . . .
H16 H 0.3828 0.1313 -0.0019 0.036 Uiso 1 1 calc R . .
C13 C 0.35024(17) 0.5203(2) 0.10800(5) 0.0325(3) Uani 1 1 d . . .
H13 H 0.3420 0.6169 0.1355 0.039 Uiso 1 1 calc R . .
C14 C 0.43380(18) 0.3377(2) 0.11815(5) 0.0390(3) Uani 1 1 d . . .
H14 H 0.4854 0.3087 0.1535 0.047 Uiso 1 1 calc R . .
C15 C 0.44468(18) 0.1940(2) 0.07772(6) 0.0371(3) Uani 1 1 d . . .
H15 H 0.5017 0.0696 0.0866 0.044 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O8 C7 1.2589(13) . ?
O9 C7 1.2703(14) . ?
O10 C6 1.3522(14) . ?
N11 C19 1.3303(15) . ?
N11 C12 1.3869(15) . ?
N18 C19 1.3293(15) . ?
N18 C17 1.3870(15) . ?
C1 C2 1.3978(15) . ?
C1 C6 1.4056(15) . ?
C1 C7 1.4929(14) . ?
C6 C5 1.3975(15) . ?
C2 C3 1.3842(16) . ?
C4 C5 1.3780(18) . ?
C4 C3 1.3928(17) . ?
C17 C16 1.3919(16) . ?
C17 C12 1.3967(15) . ?
C12 C13 1.3902(17) . ?
C16 C15 1.3772(19) . ?
C13 C14 1.3819(19) . ?
C14 C15 1.403(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 N11 C12 107.99(9) . . ?
C19 N18 C17 108.10(9) . . ?
C2 C1 C6 118.71(10) . . ?
C2 C1 C7 120.26(9) . . ?
C6 C1 C7 121.03(10) . . ?
O10 C6 C5 117.73(10) . . ?
O10 C6 C1 122.31(10) . . ?
C5 C6 C1 119.96(10) . . ?
O8 C7 O9 123.92(10) . . ?
O8 C7 C1 118.61(10) . . ?
O9 C7 C1 117.47(9) . . ?
C3 C2 C1 121.28(10) . . ?
C5 C4 C3 120.91(10) . . ?
N18 C17 C16 131.61(10) . . ?
N18 C17 C12 106.51(10) . . ?
C16 C17 C12 121.85(11) . . ?
N18 C19 N11 110.73(10) . . ?
C4 C5 C6 120.00(10) . . ?
C2 C3 C4 119.15(11) . . ?
N11 C12 C13 131.81(11) . . ?
N11 C12 C17 106.65(10) . . ?
C13 C12 C17 121.53(11) . . ?
C15 C16 C17 116.48(11) . . ?
C14 C13 C12 116.48(11) . . ?
C13 C14 C15 121.89(12) . . ?
C16 C15 C14 121.76(12) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N11 H11 O8 0.980(18) 1.651(19) 2.6220(12) 170.2(16) .
O10 H10 O9 0.84 1.81 2.5492(12) 146.2 .
N18 H18 O9 0.966(17) 1.696(18) 2.6467(13) 167.3(16) 3_565
C19 H19 O8 0.95 2.18 3.1001(15) 163.2 3_575

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        28.36
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.044
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 1451656'
_audit_update_record             
;
2016-08-13 deposited with the CCDC.
2016-09-01 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        'Adeninium salicylate monohydrate '
_chemical_name_common            '[ADE+][SA-]H2O'
_chemical_melting_point          467-472
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H13 N5 O4'
_chemical_formula_weight         291.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.9999(14)
_cell_length_b                   16.700(3)
_cell_length_c                   11.685(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.81(3)
_cell_angle_gamma                90.00
_cell_volume                     1337.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2463
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      28.45

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9780
_exptl_absorpt_correction_T_max  0.9900
_exptl_absorpt_process_details   'SADABS, Bruker 2001'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker DUO APEX II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3355
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         28.45
_reflns_number_total             3355
_reflns_number_gt                2463
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker DUO APEX II'
_computing_cell_refinement       Saint-Plus
_computing_data_reduction        Saint-Plus
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    X-Seed
_computing_publication_material  X-Seed

_refine_special_details          
;Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger., Twin
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0766P)²+0.5836P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3355
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0589
_refine_ls_wR_factor_ref         0.1574
_refine_ls_wR_factor_gt          0.1418
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N15 N 0.4362(3) -0.09985(12) 0.97134(17) 0.0264(4) Uani 1 1 d . . .
H15 H 0.5712 -0.1137 0.9935 0.057(10) Uiso 1 1 d R . .
N17 N 0.1112(3) -0.09380(12) 0.95251(18) 0.0268(4) Uani 1 1 d . . .
N11 N 0.1712(3) 0.02255(11) 0.69537(16) 0.0246(4) Uani 1 1 d . . .
H11 H 0.1063 0.0523 0.6320 0.043(8) Uiso 1 1 d R . .
N13 N 0.4781(3) -0.02138(12) 0.80284(17) 0.0257(4) Uani 1 1 d . . .
N20 N -0.1308(3) -0.00184(13) 0.73997(18) 0.0313(5) Uani 1 1 d . . .
H20A H -0.1850 0.0252 0.6771 0.038 Uiso 1 1 calc R . .
H20B H -0.2040 -0.0229 0.7850 0.038 Uiso 1 1 calc R . .
C12 C 0.3684(4) 0.01653(14) 0.7157(2) 0.0263(5) Uani 1 1 d . . .
H12 H 0.4327 0.0423 0.6617 0.032 Uiso 1 1 calc R . .
C18 C 0.1675(4) -0.05244(14) 0.86247(19) 0.0246(5) Uani 1 1 d . . .
O21 O 0.8081(3) -0.13965(12) 1.06487(17) 0.0395(5) Uani 1 1 d . . .
H21A H 0.8965 -0.1261 1.0245 0.117(19) Uiso 1 1 d R . .
H21B H 0.8358 -0.1884 1.1035 0.083(13) Uiso 1 1 d R . .
C19 C 0.0589(4) -0.01073(14) 0.76653(19) 0.0243(5) Uani 1 1 d . . .
C14 C 0.3695(3) -0.05590(13) 0.87393(19) 0.0236(5) Uani 1 1 d . . .
C16 C 0.2772(4) -0.12075(15) 1.0144(2) 0.0291(5) Uani 1 1 d . . .
H16 H 0.2851 -0.1520 1.0831 0.035 Uiso 1 1 calc R . .
O8 O -0.3057(3) 0.08050(11) 0.53905(15) 0.0334(4) Uani 1 1 d . . .
O9 O -0.0054(3) 0.11228(11) 0.51717(15) 0.0354(4) Uani 1 1 d . . .
O10 O 0.0475(3) 0.20405(12) 0.35728(17) 0.0401(5) Uani 1 1 d . . .
H10 H 0.0365 0.1654 0.4221 0.093(14) Uiso 1 1 d R . .
C1 C -0.2733(4) 0.17154(13) 0.38821(19) 0.0246(5) Uani 1 1 d . . .
C7 C -0.1932(4) 0.11762(15) 0.4888(2) 0.0269(5) Uani 1 1 d . . .
C6 C -0.1495(4) 0.21069(14) 0.3255(2) 0.0264(5) Uani 1 1 d . . .
C2 C -0.4751(4) 0.18196(15) 0.3533(2) 0.0288(5) Uani 1 1 d . . .
H2 H -0.5604 0.1557 0.3947 0.035 Uiso 1 1 calc R . .
C5 C -0.2272(4) 0.25917(15) 0.2300(2) 0.0315(6) Uani 1 1 d . . .
H5 H -0.1431 0.2856 0.1878 0.038 Uiso 1 1 calc R . .
C4 C -0.4263(4) 0.26858(16) 0.1972(2) 0.0331(6) Uani 1 1 d . . .
H4 H -0.4789 0.3014 0.1320 0.040 Uiso 1 1 calc R . .
C3 C -0.5517(4) 0.23051(16) 0.2583(2) 0.0330(6) Uani 1 1 d . . .
H3 H -0.6888 0.2377 0.2353 0.040 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N15 C14 1.355(3) . ?
N15 C16 1.357(3) . ?
N17 C16 1.316(3) . ?
N17 C18 1.382(3) . ?
N11 C12 1.355(3) . ?
N11 C19 1.373(3) . ?
N13 C12 1.306(3) . ?
N13 C14 1.363(3) . ?
N20 C19 1.309(3) . ?
C18 C14 1.394(3) . ?
C18 C19 1.404(3) . ?
O8 C7 1.240(3) . ?
O9 C7 1.291(3) . ?
O10 C6 1.357(3) . ?
C1 C2 1.398(4) . ?
C1 C6 1.405(3) . ?
C1 C7 1.496(3) . ?
C6 C5 1.396(3) . ?
C2 C3 1.390(4) . ?
C5 C4 1.377(4) . ?
C4 C3 1.393(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 N15 C16 106.5(2) . . ?
C16 N17 C18 103.4(2) . . ?
C12 N11 C19 123.5(2) . . ?
C12 N13 C14 111.6(2) . . ?
N13 C12 N11 126.0(2) . . ?
N17 C18 C14 110.4(2) . . ?
N17 C18 C19 131.6(2) . . ?
C14 C18 C19 118.0(2) . . ?
N20 C19 N11 119.3(2) . . ?
N20 C19 C18 127.1(2) . . ?
N11 C19 C18 113.6(2) . . ?
N15 C14 N13 127.0(2) . . ?
N15 C14 C18 105.7(2) . . ?
N13 C14 C18 127.2(2) . . ?
N17 C16 N15 114.0(2) . . ?
C2 C1 C6 118.9(2) . . ?
C2 C1 C7 119.9(2) . . ?
C6 C1 C7 121.2(2) . . ?
O8 C7 O9 123.8(2) . . ?
O8 C7 C1 120.0(2) . . ?
O9 C7 C1 116.2(2) . . ?
O10 C6 C5 118.3(2) . . ?
O10 C6 C1 121.3(2) . . ?
C5 C6 C1 120.4(2) . . ?
C3 C2 C1 120.5(2) . . ?
C4 C5 C6 119.7(2) . . ?
C5 C4 C3 120.9(2) . . ?
C2 C3 C4 119.7(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N20 H20A O8 0.88 1.90 2.779(3) 178.1 .
N11 H11 O9 0.93 1.73 2.656(3) 176.6 .
N15 H15 O21 0.96 1.75 2.692(3) 167.5 .
O10 H10 O9 1.01 1.50 2.502(3) 172.7 .
O21 H21A N17 0.88 1.94 2.820(3) 173.4 1_655
O21 H21B O10 0.93 1.99 2.878(3) 159.4 2_646
N20 H20B N13 0.88 2.28 2.994(3) 138.6 1_455

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        28.45
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.807
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.065
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 30:70 methanol/water'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3
_database_code_depnum_ccdc_archive 'CCDC 1451657'
_audit_update_record             
;
2016-08-13 deposited with the CCDC.
2016-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'Cytosinium salicylate '
_chemical_name_common            '[CYT+][SA-]'
_chemical_melting_point          503-511
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H11 N3 O4'
_chemical_formula_weight         249.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.6386(19)
_cell_length_b                   8.5322(17)
_cell_length_c                   13.910(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.93(3)
_cell_angle_gamma                90.00
_cell_volume                     1075.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2254
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      28.32

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9649
_exptl_absorpt_correction_T_max  0.9753
_exptl_absorpt_process_details   'SADABS, Bruker 2001'


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker DUO APEX II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8987
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         28.32
_reflns_number_total             2679
_reflns_number_gt                2254
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker DUO APEX II'
_computing_cell_refinement       Saint-Plus
_computing_data_reduction        Saint-Plus
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    X-Seed
_computing_publication_material  X-Seed

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0541P)²+0.2802P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2679
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.1053
_refine_ls_wR_factor_gt          0.0995
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N 0.13937(10) 0.17438(11) 0.11883(7) 0.0187(2) Uani 1 1 d . . .
H11 H 0.1944 0.1071 0.1042 0.040(4) Uiso 1 1 d R . .
O9 O 0.31113(9) 0.48726(10) 0.59619(6) 0.0242(2) Uani 1 1 d . . .
N13 N 0.08639(11) 0.31900(12) 0.24339(7) 0.0217(2) Uani 1 1 d . . .
H13 H 0.1140 0.3547 0.3086 0.035(4) Uiso 1 1 d R . .
C1 C 0.10113(12) 0.32190(13) 0.54906(8) 0.0187(2) Uani 1 1 d . . .
O8 O 0.19034(9) 0.45304(10) 0.43015(6) 0.02209(19) Uani 1 1 d . . .
O18 O 0.27666(9) 0.14423(10) 0.28681(6) 0.0248(2) Uani 1 1 d . . .
C6 C 0.12088(13) 0.28606(14) 0.65176(9) 0.0224(2) Uani 1 1 d . . .
C14 C -0.02544(13) 0.39266(14) 0.17014(9) 0.0232(2) Uani 1 1 d . . .
H14 H -0.0818 0.4696 0.1899 0.028 Uiso 1 1 calc R . .
O10 O 0.23097(11) 0.34951(13) 0.73096(7) 0.0333(2) Uani 1 1 d . . .
H10 H 0.2810 0.4105 0.7083 0.040 Uiso 1 1 calc R . .
N17 N 0.00972(11) 0.20567(12) -0.05213(7) 0.0234(2) Uani 1 1 d . . .
H17A H -0.0628 0.2474 -0.1030 0.036(4) Uiso 1 1 d R . .
H17B H 0.0654 0.1364 -0.0692 0.039(4) Uiso 1 1 d R . .
C5 C 0.02476(14) 0.18210(15) 0.67471(10) 0.0269(3) Uani 1 1 d . . .
H5 H 0.0395 0.1564 0.7439 0.032 Uiso 1 1 calc R . .
C12 C 0.17377(12) 0.20889(13) 0.22113(8) 0.0189(2) Uani 1 1 d . . .
C15 C -0.05826(13) 0.35906(14) 0.07006(9) 0.0216(2) Uani 1 1 d . . .
H15 H -0.1373 0.4103 0.0194 0.026 Uiso 1 1 calc R . .
C2 C -0.01927(13) 0.25594(14) 0.47261(9) 0.0216(2) Uani 1 1 d . . .
H2 H -0.0356 0.2815 0.4031 0.026 Uiso 1 1 calc R . .
C16 C 0.02897(12) 0.24461(13) 0.04266(8) 0.0185(2) Uani 1 1 d . . .
C4 C -0.09144(14) 0.11658(15) 0.59753(10) 0.0271(3) Uani 1 1 d . . .
H4 H -0.1557 0.0452 0.6139 0.033 Uiso 1 1 calc R . .
C7 C 0.20656(12) 0.42793(13) 0.52309(8) 0.0184(2) Uani 1 1 d . . .
C3 C -0.11520(14) 0.15445(15) 0.49571(10) 0.0260(3) Uani 1 1 d . . .
H3 H -0.1965 0.1109 0.4427 0.031 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 C16 1.3584(15) . ?
N11 C12 1.3784(14) . ?
O9 C7 1.2678(14) . ?
N13 C14 1.3588(16) . ?
N13 C12 1.3659(15) . ?
C1 C2 1.3975(17) . ?
C1 C6 1.4089(16) . ?
C1 C7 1.4940(15) . ?
O8 C7 1.2664(13) . ?
O18 C12 1.2268(14) . ?
C6 O10 1.3549(15) . ?
C6 C5 1.3960(17) . ?
C14 C15 1.3491(17) . ?
N17 C16 1.3101(15) . ?
C5 C4 1.3783(19) . ?
C15 C16 1.4228(16) . ?
C2 C3 1.3822(17) . ?
C4 C3 1.3935(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 N11 C12 124.04(10) . . ?
C14 N13 C12 122.75(10) . . ?
C2 C1 C6 118.31(11) . . ?
C2 C1 C7 121.11(10) . . ?
C6 C1 C7 120.58(11) . . ?
O10 C6 C5 117.70(11) . . ?
O10 C6 C1 122.37(11) . . ?
C5 C6 C1 119.93(11) . . ?
C15 C14 N13 121.50(11) . . ?
C4 C5 C6 120.40(11) . . ?
O18 C12 N13 123.02(10) . . ?
O18 C12 N11 121.45(11) . . ?
N13 C12 N11 115.53(10) . . ?
C14 C15 C16 118.04(11) . . ?
C3 C2 C1 121.55(11) . . ?
N17 C16 N11 118.53(10) . . ?
N17 C16 C15 123.35(11) . . ?
N11 C16 C15 118.11(10) . . ?
C5 C4 C3 120.40(12) . . ?
O8 C7 O9 122.61(10) . . ?
O8 C7 C1 119.46(10) . . ?
O9 C7 C1 117.91(10) . . ?
C2 C3 C4 119.36(12) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N13 H13 O8 0.91 1.80 2.6993(14) 168.7 .
O10 H10 O9 0.84 1.80 2.5456(13) 146.2 .
N11 H11 O8 0.85 1.88 2.7363(13) 177.8 2_545
N17 H17B O9 0.88 1.87 2.7480(14) 176.2 2_545
N17 H17A O18 0.88 2.00 2.8766(16) 176.1 4_565

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        28.32
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.047
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 30:70 dioxane/water'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4
_database_code_depnum_ccdc_archive 'CCDC 1451658'
_audit_update_record             
;
2016-08-13 deposited with the CCDC.
2016-09-01 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'Di-benzimidazolium sulfosalicylate monohydrate '
_chemical_name_common            2[BIM+][SSA-2]H2O
_chemical_melting_point          519-521
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H20 N4 O7 S'
_chemical_formula_weight         472.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.909(2)
_cell_length_b                   9.817(2)
_cell_length_c                   22.872(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.12(3)
_cell_angle_gamma                90.00
_cell_volume                     2175.4(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4571
_cell_measurement_theta_min      1.82
_cell_measurement_theta_max      28.39

_exptl_crystal_description       blocks
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.33
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9222
_exptl_absorpt_correction_T_max  0.9367
_exptl_absorpt_process_details   'SADABS, Bruker 2001'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker DUO APEX II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            28772
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         28.39
_reflns_number_total             5450
_reflns_number_gt                4571
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker DUO APEX II'
_computing_cell_refinement       Saint-Plus
_computing_data_reduction        Saint-Plus
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    X-Seed
_computing_publication_material  X-Seed

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0512P)²+0.8547P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5450
_refine_ls_number_parameters     305
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1070
_refine_ls_wR_factor_gt          0.1012
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.24852(3) 0.41143(4) 0.116367(15) 0.02441(10) Uani 1 1 d . . .
C1 C 0.61577(13) 0.59389(14) 0.18014(6) 0.0214(3) Uani 1 1 d . . .
C2 C 0.48849(13) 0.55752(13) 0.14425(6) 0.0210(3) Uani 1 1 d . . .
H2 H 0.4548 0.6050 0.1079 0.025 Uiso 1 1 calc R . .
C3 C 0.41120(13) 0.45278(14) 0.16123(6) 0.0217(3) Uani 1 1 d . . .
C4 C 0.45965(15) 0.38271(15) 0.21464(6) 0.0271(3) Uani 1 1 d . . .
H4 H 0.4066 0.3108 0.2261 0.032 Uiso 1 1 calc R . .
C5 C 0.58466(16) 0.41786(15) 0.25081(6) 0.0290(3) Uani 1 1 d . . .
H5 H 0.6170 0.3704 0.2873 0.035 Uiso 1 1 calc R . .
C6 C 0.66368(14) 0.52263(15) 0.23410(6) 0.0244(3) Uani 1 1 d . . .
C7 C 0.70072(14) 0.70473(15) 0.16112(6) 0.0264(3) Uani 1 1 d . . .
O8 O 0.65628(11) 0.76463(12) 0.11195(5) 0.0355(3) Uani 1 1 d . . .
O9 O 0.81380(12) 0.73465(13) 0.19530(5) 0.0416(3) Uani 1 1 d . . .
O10 O 0.78646(11) 0.55257(12) 0.27006(5) 0.0333(3) Uani 1 1 d . . .
H10 H 0.8163 0.6254 0.2488 0.070(7) Uiso 1 1 d R . .
O11 O 0.22207(14) 0.27148(12) 0.13017(6) 0.0481(3) Uani 1 1 d . . .
O12 O 0.25889(11) 0.43188(12) 0.05443(4) 0.0325(2) Uani 1 1 d . . .
O13 O 0.14990(11) 0.50664(13) 0.13319(5) 0.0379(3) Uani 1 1 d . . .
O20 O 0.44499(12) 0.29108(16) 0.00349(5) 0.0513(4) Uani 1 1 d . . .
H20B H 0.4168 0.2840 -0.0338 0.068(7) Uiso 1 1 d R . .
H20A H 0.3816 0.3282 0.0175 0.068(8) Uiso 1 1 d R . .
H18A H 1.0937 1.1235 0.1134 0.051(6) Uiso 1 1 d R . .
N11A N 0.84243(13) 0.94269(13) 0.09059(5) 0.0274(3) Uani 1 1 d . . .
H11A H 0.7783 0.8780 0.0999 0.069(7) Uiso 1 1 d R . .
C12A C 0.82098(15) 1.02195(15) 0.03920(6) 0.0268(3) Uani 1 1 d . . .
C13A C 0.71270(17) 1.02587(18) -0.01063(7) 0.0360(3) Uani 1 1 d . . .
H13A H 0.6354 0.9667 -0.0146 0.043 Uiso 1 1 calc R . .
C14A C 0.7242(2) 1.1207(2) -0.05381(8) 0.0452(4) Uani 1 1 d . . .
H14A H 0.6522 1.1277 -0.0884 0.054 Uiso 1 1 calc R . .
C15A C 0.8390(2) 1.20715(18) -0.04820(8) 0.0461(5) Uani 1 1 d . . .
H15A H 0.8427 1.2704 -0.0793 0.055 Uiso 1 1 calc R . .
C16A C 0.9461(2) 1.20304(16) 0.00088(8) 0.0387(4) Uani 1 1 d . . .
H16A H 1.0238 1.2614 0.0045 0.046 Uiso 1 1 calc R . .
C17A C 0.93472(15) 1.10872(14) 0.04514(7) 0.0284(3) Uani 1 1 d . . .
N18A N 1.01968(13) 1.07833(13) 0.09974(6) 0.0307(3) Uani 1 1 d . . .
C19A C 0.96130(15) 0.97990(15) 0.12546(7) 0.0296(3) Uani 1 1 d . . .
H19A H 0.9992 0.9414 0.1635 0.036 Uiso 1 1 calc R . .
N11B N -0.11447(12) 0.41819(13) 0.11854(6) 0.0281(3) Uani 1 1 d . . .
H11B H -0.0300 0.4604 0.1232 0.056(6) Uiso 1 1 d R . .
C12B C -0.15143(14) 0.32223(15) 0.15651(6) 0.0264(3) Uani 1 1 d . . .
C13B C -0.08223(19) 0.2782(2) 0.21259(7) 0.0418(4) Uani 1 1 d . . .
H13B H 0.0041 0.3158 0.2318 0.050 Uiso 1 1 calc R . .
C14B C -0.1444(3) 0.1790(2) 0.23837(9) 0.0573(6) Uani 1 1 d . . .
H14B H -0.1007 0.1461 0.2767 0.069 Uiso 1 1 calc R . .
C15B C -0.2704(3) 0.1239(2) 0.21023(11) 0.0646(7) Uani 1 1 d . . .
H15B H -0.3092 0.0534 0.2299 0.078 Uiso 1 1 calc R . .
C16B C -0.3428(2) 0.16803(19) 0.15409(10) 0.0477(5) Uani 1 1 d . . .
H16B H -0.4296 0.1308 0.1353 0.057 Uiso 1 1 calc R . .
C17B C -0.27860(15) 0.27020(15) 0.12776(6) 0.0272(3) Uani 1 1 d . . .
N18B N -0.31304(12) 0.33776(14) 0.07332(5) 0.0290(3) Uani 1 1 d . . .
H18B H -0.3994 0.3234 0.0451 0.066(7) Uiso 1 1 d R . .
C19B C -0.21316(16) 0.42300(16) 0.06944(7) 0.0298(3) Uani 1 1 d . . .
H19B H -0.2118 0.4802 0.0361 0.036 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O11 1.4459(12) . ?
S1 O12 1.4555(11) . ?
S1 O13 1.4610(12) . ?
S1 C3 1.7669(14) . ?
C1 C2 1.3990(18) . ?
C1 C6 1.4113(19) . ?
C1 C7 1.4951(19) . ?
C2 C3 1.3855(18) . ?
C3 C4 1.3964(19) . ?
C4 C5 1.381(2) . ?
C5 C6 1.394(2) . ?
C6 O10 1.3502(17) . ?
C7 O9 1.2590(17) . ?
C7 O8 1.2636(18) . ?
N11A C19A 1.3276(19) . ?
N11A C12A 1.3883(19) . ?
C12A C13A 1.392(2) . ?
C12A C17A 1.396(2) . ?
C13A C14A 1.379(2) . ?
C14A C15A 1.403(3) . ?
C15A C16A 1.374(3) . ?
C16A C17A 1.394(2) . ?
C17A N18A 1.384(2) . ?
N18A C19A 1.326(2) . ?
N11B C19B 1.3261(19) . ?
N11B C12B 1.382(2) . ?
C12B C13B 1.390(2) . ?
C12B C17B 1.390(2) . ?
C13B C14B 1.352(3) . ?
C14B C15B 1.389(4) . ?
C15B C16B 1.401(3) . ?
C16B C17B 1.391(2) . ?
C17B N18B 1.3886(19) . ?
N18B C19B 1.313(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S1 O12 113.37(8) . . ?
O11 S1 O13 112.85(8) . . ?
O12 S1 O13 110.85(7) . . ?
O11 S1 C3 106.06(7) . . ?
O12 S1 C3 106.93(7) . . ?
O13 S1 C3 106.22(7) . . ?
C2 C1 C6 118.87(12) . . ?
C2 C1 C7 120.56(12) . . ?
C6 C1 C7 120.56(12) . . ?
C3 C2 C1 120.55(12) . . ?
C2 C3 C4 120.14(12) . . ?
C2 C3 S1 119.89(10) . . ?
C4 C3 S1 119.94(11) . . ?
C5 C4 C3 120.08(13) . . ?
C4 C5 C6 120.33(13) . . ?
O10 C6 C5 118.67(12) . . ?
O10 C6 C1 121.30(13) . . ?
C5 C6 C1 120.03(12) . . ?
O9 C7 O8 122.85(14) . . ?
O9 C7 C1 118.12(13) . . ?
O8 C7 C1 119.03(12) . . ?
C19A N11A C12A 108.26(12) . . ?
N11A C12A C13A 131.55(14) . . ?
N11A C12A C17A 106.41(13) . . ?
C13A C12A C17A 122.03(15) . . ?
C14A C13A C12A 116.07(16) . . ?
C13A C14A C15A 122.00(17) . . ?
C16A C15A C14A 121.95(16) . . ?
C15A C16A C17A 116.53(16) . . ?
N18A C17A C16A 132.22(15) . . ?
N18A C17A C12A 106.38(13) . . ?
C16A C17A C12A 121.41(16) . . ?
C19A N18A C17A 108.55(12) . . ?
N18A C19A N11A 110.41(14) . . ?
C19B N11B C12B 108.11(12) . . ?
N11B C12B C13B 130.33(15) . . ?
N11B C12B C17B 106.66(12) . . ?
C13B C12B C17B 123.00(16) . . ?
C14B C13B C12B 116.40(19) . . ?
C13B C14B C15B 121.74(18) . . ?
C14B C15B C16B 122.80(18) . . ?
C17B C16B C15B 115.27(19) . . ?
N18B C17B C12B 106.04(13) . . ?
N18B C17B C16B 133.16(16) . . ?
C12B C17B C16B 120.78(16) . . ?
C19B N18B C17B 108.55(12) . . ?
N18B C19B N11B 110.63(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.4(2) . . . . ?
C7 C1 C2 C3 178.56(13) . . . . ?
C1 C2 C3 C4 0.3(2) . . . . ?
C1 C2 C3 S1 178.25(10) . . . . ?
O11 S1 C3 C2 156.62(12) . . . . ?
O12 S1 C3 C2 35.35(13) . . . . ?
O13 S1 C3 C2 -83.07(13) . . . . ?
O11 S1 C3 C4 -25.38(14) . . . . ?
O12 S1 C3 C4 -146.65(12) . . . . ?
O13 S1 C3 C4 94.92(13) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
S1 C3 C4 C5 -177.82(12) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C4 C5 C6 O10 -178.86(14) . . . . ?
C4 C5 C6 C1 0.3(2) . . . . ?
C2 C1 C6 O10 179.26(12) . . . . ?
C7 C1 C6 O10 0.3(2) . . . . ?
C2 C1 C6 C5 0.1(2) . . . . ?
C7 C1 C6 C5 -178.85(13) . . . . ?
C2 C1 C7 O9 179.24(14) . . . . ?
C6 C1 C7 O9 -1.8(2) . . . . ?
C2 C1 C7 O8 -0.4(2) . . . . ?
C6 C1 C7 O8 178.51(14) . . . . ?
C19A N11A C12A C13A -178.76(16) . . . . ?
C19A N11A C12A C17A 0.31(16) . . . . ?
N11A C12A C13A C14A 178.87(16) . . . . ?
C17A C12A C13A C14A -0.1(2) . . . . ?
C12A C13A C14A C15A 0.7(3) . . . . ?
C13A C14A C15A C16A -0.5(3) . . . . ?
C14A C15A C16A C17A -0.3(2) . . . . ?
C15A C16A C17A N18A -178.92(16) . . . . ?
C15A C16A C17A C12A 0.9(2) . . . . ?
N11A C12A C17A N18A -0.06(15) . . . . ?
C13A C12A C17A N18A 179.12(14) . . . . ?
N11A C12A C17A C16A -179.89(13) . . . . ?
C13A C12A C17A C16A -0.7(2) . . . . ?
C16A C17A N18A C19A 179.58(16) . . . . ?
C12A C17A N18A C19A -0.22(16) . . . . ?
C17A N18A C19A N11A 0.43(17) . . . . ?
C12A N11A C19A N18A -0.47(17) . . . . ?
C19B N11B C12B C13B 178.85(16) . . . . ?
C19B N11B C12B C17B -0.49(16) . . . . ?
N11B C12B C13B C14B -178.41(16) . . . . ?
C17B C12B C13B C14B 0.8(2) . . . . ?
C12B C13B C14B C15B 0.1(3) . . . . ?
C13B C14B C15B C16B -1.0(3) . . . . ?
C14B C15B C16B C17B 0.9(3) . . . . ?
N11B C12B C17B N18B -0.07(15) . . . . ?
C13B C12B C17B N18B -179.47(14) . . . . ?
N11B C12B C17B C16B 178.45(14) . . . . ?
C13B C12B C17B C16B -0.9(2) . . . . ?
C15B C16B C17B N18B 178.13(16) . . . . ?
C15B C16B C17B C12B 0.1(2) . . . . ?
C12B C17B N18B C19B 0.62(16) . . . . ?
C16B C17B N18B C19B -177.64(17) . . . . ?
C17B N18B C19B N11B -0.96(17) . . . . ?
C12B N11B C19B N18B 0.91(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N11A H11A O8 0.95 1.71 2.6599(16) 176.1 .
N11B H11B O13 0.92 1.81 2.7131(17) 167.8 .
O10 H10 O9 0.95 1.62 2.5273(17) 158.4 .
O20 H20A O12 0.85 1.91 2.7516(18) 171.4 .
N18B H18B O20 0.97 1.66 2.6272(18) 173.0 1_455
N18A H18A O11 0.86 1.92 2.7415(17) 161.1 1_665
O20 H20B O8 0.84 1.84 2.6767(17) 168.8 3_665

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        28.39
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.047
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 30:70 acetonitrile/water'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5
_database_code_depnum_ccdc_archive 'CCDC 1451659'
_audit_update_record             
;
2016-08-13 deposited with the CCDC.
2016-09-01 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        'Adeninium sulfosalicylate monohydrate '
_chemical_name_common            '[ADE+][SSA-]H2O'
_chemical_melting_point          439-441
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H13 N5 O7 S'
_chemical_formula_weight         371.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7311(13)
_cell_length_b                   10.314(2)
_cell_length_c                   10.743(2)
_cell_angle_alpha                85.32(3)
_cell_angle_beta                 85.11(3)
_cell_angle_gamma                86.41(3)
_cell_volume                     739.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2671
_cell_measurement_theta_min      1.91
_cell_measurement_theta_max      27.55

_exptl_crystal_description       plates
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9158
_exptl_absorpt_correction_T_max  0.9866
_exptl_absorpt_process_details   'SADABS, Bruker 2001'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker DUO APEX II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5117
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0497
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         27.55
_reflns_number_total             3406
_reflns_number_gt                2671
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker DUO APEX II'
_computing_cell_refinement       Saint-Plus
_computing_data_reduction        Saint-Plus
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    X-Seed
_computing_publication_material  X-Seed

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0564P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3406
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1098
_refine_ls_wR_factor_gt          0.1018
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.29466(7) 0.58972(5) 0.78213(5) 0.02050(14) Uani 1 1 d . . .
C1 C 0.3370(3) 0.20558(18) 0.72077(18) 0.0167(4) Uani 1 1 d . . .
C2 C 0.3120(3) 0.34225(19) 0.70453(18) 0.0178(4) Uani 1 1 d . . .
H2 H 0.2820 0.3830 0.6253 0.021 Uiso 1 1 calc R . .
C3 C 0.3309(3) 0.41783(19) 0.80320(18) 0.0181(4) Uani 1 1 d . . .
C4 C 0.3799(3) 0.35739(19) 0.91933(19) 0.0202(4) Uani 1 1 d . . .
H4 H 0.3928 0.4091 0.9871 0.024 Uiso 1 1 calc R . .
C5 C 0.4095(3) 0.2240(2) 0.93609(19) 0.0198(4) Uani 1 1 d . . .
H5 H 0.4470 0.1844 1.0142 0.024 Uiso 1 1 calc R . .
C6 C 0.3843(3) 0.14650(19) 0.83768(19) 0.0188(4) Uani 1 1 d . . .
C7 C 0.3057(3) 0.12572(19) 0.61710(19) 0.0178(4) Uani 1 1 d . . .
O8 O 0.2541(2) 0.19118(15) 0.51577(14) 0.0251(3) Uani 1 1 d . . .
H8 H 0.238(4) 0.138(3) 0.456(3) 0.066(10) Uiso 1 1 d . . .
H21A H 0.908(5) 0.556(3) 0.639(3) 0.061(10) Uiso 1 1 d . . .
O9 O 0.3266(2) 0.00469(13) 0.62824(14) 0.0237(3) Uani 1 1 d . . .
O10 O 0.4043(2) 0.01520(14) 0.86075(15) 0.0240(3) Uani 1 1 d . . .
H10 H 0.388(4) -0.017(3) 0.785(3) 0.052(9) Uiso 1 1 d . . .
O11 O 0.4926(2) 0.64060(15) 0.76340(17) 0.0350(4) Uani 1 1 d . . .
N11 N 0.1740(2) -0.27834(16) 0.28273(16) 0.0185(4) Uani 1 1 d . . .
H11 H 0.187(4) -0.366(3) 0.319(3) 0.053(8) Uiso 1 1 d . . .
H21B H 0.716(5) 0.564(3) 0.666(3) 0.058(10) Uiso 1 1 d . . .
O12 O 0.1821(2) 0.63080(15) 0.89364(15) 0.0337(4) Uani 1 1 d . . .
C12 C 0.1226(3) -0.26244(19) 0.16248(19) 0.0189(4) Uani 1 1 d . . .
H12 H 0.1144 -0.3388 0.1198 0.023 Uiso 1 1 calc R . .
O13 O 0.1840(2) 0.61374(13) 0.66982(13) 0.0246(3) Uani 1 1 d . . .
N13 N 0.0835(2) -0.15016(16) 0.10082(15) 0.0184(3) Uani 1 1 d . . .
C14 C 0.1027(3) -0.04789(19) 0.17014(18) 0.0169(4) Uani 1 1 d . . .
N15 N 0.0678(2) 0.08092(16) 0.13579(16) 0.0201(4) Uani 1 1 d . . .
H15 H 0.027(3) 0.115(2) 0.063(2) 0.034(7) Uiso 1 1 d . . .
H20A H 0.244(3) -0.277(3) 0.515(2) 0.035(7) Uiso 1 1 d . . .
C16 C 0.1096(3) 0.1470(2) 0.23306(19) 0.0216(4) Uani 1 1 d . . .
H16 H 0.0984 0.2393 0.2324 0.026 Uiso 1 1 calc R . .
H20B H 0.2623 -0.1293 0.5160 0.032(7) Uiso 1 1 d R . .
N17 N 0.1673(2) 0.07046(16) 0.32853(16) 0.0202(4) Uani 1 1 d . . .
C18 C 0.1626(3) -0.05340(19) 0.29028(18) 0.0175(4) Uani 1 1 d . . .
C19 C 0.1971(3) -0.17721(19) 0.35406(18) 0.0174(4) Uani 1 1 d . . .
N20 N 0.2459(2) -0.19704(17) 0.46997(16) 0.0199(4) Uani 1 1 d . . .
O21 O 0.8077(3) 0.52175(16) 0.62374(18) 0.0328(4) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O12 1.4411(17) . ?
S1 O11 1.4545(16) . ?
S1 O13 1.4673(15) . ?
S1 C3 1.773(2) . ?
C1 C6 1.403(3) . ?
C1 C2 1.408(3) . ?
C1 C7 1.475(3) . ?
C2 C3 1.385(3) . ?
C3 C4 1.404(3) . ?
C4 C5 1.377(3) . ?
C5 C6 1.404(3) . ?
C6 O10 1.357(2) . ?
C7 O9 1.245(2) . ?
C7 O8 1.295(2) . ?
N11 C12 1.360(3) . ?
N11 C19 1.368(3) . ?
C12 N13 1.310(2) . ?
N13 C14 1.359(3) . ?
C14 N15 1.361(2) . ?
C14 C18 1.380(3) . ?
N15 C16 1.352(3) . ?
C16 N17 1.313(3) . ?
N17 C18 1.377(3) . ?
C18 C19 1.415(3) . ?
C19 N20 1.311(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O12 S1 O11 113.16(11) . . ?
O12 S1 O13 112.91(9) . . ?
O11 S1 O13 112.11(10) . . ?
O12 S1 C3 106.59(10) . . ?
O11 S1 C3 106.46(9) . . ?
O13 S1 C3 104.87(9) . . ?
C6 C1 C2 119.30(18) . . ?
C6 C1 C7 120.62(17) . . ?
C2 C1 C7 120.03(17) . . ?
C3 C2 C1 120.51(18) . . ?
C2 C3 C4 119.53(18) . . ?
C2 C3 S1 120.01(15) . . ?
C4 C3 S1 120.46(15) . . ?
C5 C4 C3 120.75(19) . . ?
C4 C5 C6 120.00(18) . . ?
O10 C6 C1 122.28(19) . . ?
O10 C6 C5 117.85(17) . . ?
C1 C6 C5 119.86(18) . . ?
O9 C7 O8 123.43(18) . . ?
O9 C7 C1 121.71(17) . . ?
O8 C7 C1 114.86(17) . . ?
C12 N11 C19 123.74(17) . . ?
N13 C12 N11 125.18(19) . . ?
C12 N13 C14 112.31(17) . . ?
N13 C14 N15 127.33(18) . . ?
N13 C14 C18 126.94(18) . . ?
N15 C14 C18 105.72(17) . . ?
C16 N15 C14 106.76(17) . . ?
N17 C16 N15 113.03(18) . . ?
C16 N17 C18 104.38(17) . . ?
N17 C18 C14 110.10(17) . . ?
N17 C18 C19 131.40(18) . . ?
C14 C18 C19 118.40(18) . . ?
N20 C19 N11 121.71(18) . . ?
N20 C19 C18 124.99(19) . . ?
N11 C19 C18 113.30(17) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N20 H20B O9 0.91 2.00 2.897(2) 172.3 .
O10 H10 O9 0.92(3) 1.76(3) 2.607(2) 151(3) .
O21 H21B O11 0.86(3) 1.92(3) 2.772(3) 173(3) .
O8 H8 N17 0.90(3) 1.70(3) 2.576(2) 165(3) .
N15 H15 N13 0.89(3) 1.97(3) 2.839(2) 167(2) 2
N20 H20A O13 0.92(3) 1.96(3) 2.803(2) 151(2) 1_545
N11 H11 O21 0.96(3) 1.67(3) 2.627(2) 175(3) 2_656

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.063
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 30:70 methanol/water'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_6
_database_code_depnum_ccdc_archive 'CCDC 1451660'
_audit_update_record             
;
2016-08-13 deposited with the CCDC.
2016-09-01 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'Cytosinium sulfosalicylate cytosine monohydrate '
_chemical_name_common            '[CYT+][SAA-][CYT]H2O'
_chemical_melting_point          496-500
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H18 N6 O9 S'
_chemical_formula_weight         458.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2974(15)
_cell_length_b                   8.4044(17)
_cell_length_c                   15.470(3)
_cell_angle_alpha                77.82(3)
_cell_angle_beta                 83.19(3)
_cell_angle_gamma                88.82(3)
_cell_volume                     920.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3184
_cell_measurement_theta_min      1.36
_cell_measurement_theta_max      28.54

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             476
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.000
_exptl_absorpt_correction_T_max  0.791
_exptl_absorpt_process_details   'SADABS, Bruker 2001'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker DUO APEX II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15137
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_sigmaI/netI    0.0685
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.36
_diffrn_reflns_theta_max         28.54
_reflns_number_total             4613
_reflns_number_gt                3184
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker DUO APEX II'
_computing_cell_refinement       Saint-Plus
_computing_data_reduction        Saint-Plus
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    X-Seed
_computing_publication_material  X-Seed

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0649P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       noref
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4613
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1256
_refine_ls_wR_factor_gt          0.1088
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.24764(7) 0.33556(6) 0.16549(3) 0.02239(15) Uani 1 1 d . . .
C1 C 0.2564(3) -0.0011(2) 0.01492(12) 0.0221(4) Uani 1 1 d . . .
C2 C 0.2654(3) 0.0765(3) 0.08591(13) 0.0235(4) Uani 1 1 d . . .
H2 H 0.2938 0.0153 0.1417 0.028 Uiso 1 1 calc R . .
C3 C 0.2336(3) 0.2404(3) 0.07538(12) 0.0223(4) Uani 1 1 d . . .
C4 C 0.1916(3) 0.3319(3) -0.00635(13) 0.0256(4) Uani 1 1 d . . .
H4 H 0.1710 0.4457 -0.0135 0.031 Uiso 1 1 calc R . .
C5 C 0.1803(3) 0.2567(3) -0.07658(13) 0.0272(5) Uani 1 1 d . . .
H5 H 0.1501 0.3183 -0.1319 0.033 Uiso 1 1 calc R . .
C6 C 0.2132(3) 0.0905(3) -0.06643(12) 0.0246(5) Uani 1 1 d . . .
C7 C 0.2905(3) -0.1769(3) 0.02561(13) 0.0241(4) Uani 1 1 d . . .
O8 O 0.3337(2) -0.2470(2) 0.10511(10) 0.0324(4) Uani 1 1 d . . .
H8 H 0.357(4) -0.362(4) 0.1080(18) 0.062(9) Uiso 1 1 d . . .
H13B H -0.150(3) 0.011(3) 0.4266(14) 0.023(6) Uiso 1 1 d . . .
H13A H -0.364(4) -0.003(4) 0.5852(16) 0.043(8) Uiso 1 1 d . . .
H11A H -0.289(4) 0.453(4) 0.5265(17) 0.050(8) Uiso 1 1 d . . .
H19B H -0.177(4) 0.332(4) 0.2003(18) 0.051(9) Uiso 1 1 d . . .
H19A H -0.334(4) 0.335(4) 0.175(2) 0.056(9) Uiso 1 1 d . . .
O9 O 0.2785(2) -0.25047(19) -0.03357(9) 0.0310(4) Uani 1 1 d . . .
O10 O 0.2036(2) 0.0228(2) -0.13798(9) 0.0322(4) Uani 1 1 d . . .
H10 H 0.218(5) -0.090(5) -0.115(2) 0.076(11) Uiso 1 1 d . . .
O11 O 0.4076(2) 0.44553(18) 0.13997(9) 0.0265(3) Uani 1 1 d . . .
O12 O 0.2698(2) 0.20938(18) 0.24242(9) 0.0307(4) Uani 1 1 d . . .
O13 O 0.0771(2) 0.4282(2) 0.17478(9) 0.0299(4) Uani 1 1 d . . .
O19 O -0.2884(3) 0.3078(3) 0.22528(12) 0.0440(5) Uani 1 1 d . . .
N11A N -0.3437(2) 0.3681(2) 0.56504(11) 0.0229(4) Uani 1 1 d . . .
C12A C -0.3083(3) 0.2199(3) 0.54270(12) 0.0232(4) Uani 1 1 d . . .
N13A N -0.3843(3) 0.0877(2) 0.60149(11) 0.0243(4) Uani 1 1 d . . .
C14A C -0.4873(3) 0.1005(3) 0.67942(13) 0.0254(5) Uani 1 1 d . . .
H14A H -0.5365 0.0047 0.7189 0.031 Uiso 1 1 calc R . .
C15A C -0.5205(3) 0.2457(3) 0.70152(13) 0.0255(5) Uani 1 1 d . . .
H15A H -0.5920 0.2532 0.7560 0.031 Uiso 1 1 calc R . .
C16A C -0.4458(3) 0.3878(3) 0.64127(12) 0.0232(4) Uani 1 1 d . . .
N17A N -0.4705(3) 0.5347(2) 0.65476(11) 0.0293(4) Uani 1 1 d . . .
H17A H -0.4216 0.6182 0.6150 0.035 Uiso 1 1 calc R . .
H17B H -0.5362 0.5506 0.7037 0.035 Uiso 1 1 calc R . .
O18A O -0.2114(2) 0.21033(18) 0.47322(9) 0.0290(4) Uani 1 1 d . . .
N11B N -0.1695(2) -0.3594(2) 0.44586(10) 0.0224(4) Uani 1 1 d . . .
C12B C -0.2027(3) -0.2124(3) 0.46635(12) 0.0230(4) Uani 1 1 d . . .
N13B N -0.1313(3) -0.0755(2) 0.40901(11) 0.0257(4) Uani 1 1 d . . .
C14B C -0.0283(3) -0.0820(3) 0.33075(13) 0.0270(5) Uani 1 1 d . . .
H14B H 0.0192 0.0156 0.2923 0.032 Uiso 1 1 calc R . .
C15B C 0.0066(3) -0.2253(3) 0.30757(12) 0.0254(5) Uani 1 1 d . . .
H15B H 0.0779 -0.2319 0.2529 0.031 Uiso 1 1 calc R . .
C16B C -0.0675(3) -0.3678(3) 0.36816(12) 0.0222(4) Uani 1 1 d . . .
N17B N -0.0380(3) -0.5131(2) 0.34982(11) 0.0298(4) Uani 1 1 d . . .
H17C H -0.0842 -0.6002 0.3876 0.036 Uiso 1 1 calc R . .
H17D H 0.0279 -0.5229 0.2998 0.036 Uiso 1 1 calc R . .
O18B O -0.3004(2) -0.19828(18) 0.53678(9) 0.0288(4) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O12 1.4397(16) . ?
S1 O13 1.4633(17) . ?
S1 O11 1.4673(15) . ?
S1 C3 1.761(2) . ?
C1 C6 1.397(3) . ?
C1 C2 1.399(3) . ?
C1 C7 1.472(3) . ?
C2 C3 1.371(3) . ?
C3 C4 1.398(3) . ?
C4 C5 1.379(3) . ?
C5 C6 1.391(3) . ?
C6 O10 1.356(2) . ?
C7 O9 1.220(2) . ?
C7 O8 1.318(2) . ?
N11A C16A 1.357(3) . ?
N11A C12A 1.373(3) . ?
C12A O18A 1.231(2) . ?
C12A N13A 1.360(3) . ?
N13A C14A 1.366(3) . ?
C14A C15A 1.345(3) . ?
C15A C16A 1.425(3) . ?
C16A N17A 1.300(3) . ?
N11B C12B 1.349(3) . ?
N11B C16B 1.351(2) . ?
C12B O18B 1.256(2) . ?
C12B N13B 1.366(3) . ?
N13B C14B 1.358(3) . ?
C14B C15B 1.339(3) . ?
C15B C16B 1.428(3) . ?
C16B N17B 1.318(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O12 S1 O13 113.37(10) . . ?
O12 S1 O11 112.44(10) . . ?
O13 S1 O11 110.53(9) . . ?
O12 S1 C3 107.39(10) . . ?
O13 S1 C3 106.38(10) . . ?
O11 S1 C3 106.25(9) . . ?
C6 C1 C2 119.09(19) . . ?
C6 C1 C7 120.23(17) . . ?
C2 C1 C7 120.67(18) . . ?
C3 C2 C1 120.31(19) . . ?
C2 C3 C4 120.45(18) . . ?
C2 C3 S1 119.46(15) . . ?
C4 C3 S1 120.09(17) . . ?
C5 C4 C3 119.8(2) . . ?
C4 C5 C6 120.01(19) . . ?
O10 C6 C5 117.75(19) . . ?
O10 C6 C1 121.9(2) . . ?
C5 C6 C1 120.31(18) . . ?
O9 C7 O8 123.4(2) . . ?
O9 C7 C1 122.90(19) . . ?
O8 C7 C1 113.66(17) . . ?
C16A N11A C12A 124.00(18) . . ?
O18A C12A N13A 123.0(2) . . ?
O18A C12A N11A 120.69(18) . . ?
N13A C12A N11A 116.33(18) . . ?
C12A N13A C14A 122.07(19) . . ?
C15A C14A N13A 121.48(19) . . ?
C14A C15A C16A 118.35(19) . . ?
N17A C16A N11A 118.30(18) . . ?
N17A C16A C15A 123.95(19) . . ?
N11A C16A C15A 117.75(19) . . ?
C12B N11B C16B 119.06(17) . . ?
O18B C12B N11B 121.29(18) . . ?
O18B C12B N13B 119.04(19) . . ?
N11B C12B N13B 119.66(17) . . ?
C14B N13B C12B 122.01(19) . . ?
C15B C14B N13B 120.22(19) . . ?
C14B C15B C16B 117.41(18) . . ?
N17B C16B N11B 117.66(18) . . ?
N17B C16B C15B 120.70(18) . . ?
N11B C16B C15B 121.64(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.5(3) . . . . ?
C7 C1 C2 C3 179.94(18) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C1 C2 C3 S1 -179.49(15) . . . . ?
O12 S1 C3 C2 -7.4(2) . . . . ?
O13 S1 C3 C2 -129.09(17) . . . . ?
O11 S1 C3 C2 113.11(17) . . . . ?
O12 S1 C3 C4 173.07(16) . . . . ?
O13 S1 C3 C4 51.38(18) . . . . ?
O11 S1 C3 C4 -66.41(19) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
S1 C3 C4 C5 -179.82(16) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C4 C5 C6 O10 -178.83(19) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C2 C1 C6 O10 179.49(18) . . . . ?
C7 C1 C6 O10 -0.9(3) . . . . ?
C2 C1 C6 C5 0.2(3) . . . . ?
C7 C1 C6 C5 179.82(19) . . . . ?
C6 C1 C7 O9 -1.9(3) . . . . ?
C2 C1 C7 O9 177.64(19) . . . . ?
C6 C1 C7 O8 178.59(18) . . . . ?
C2 C1 C7 O8 -1.8(3) . . . . ?
C16A N11A C12A O18A -178.51(19) . . . . ?
C16A N11A C12A N13A 0.9(3) . . . . ?
O18A C12A N13A C14A 178.2(2) . . . . ?
N11A C12A N13A C14A -1.2(3) . . . . ?
C12A N13A C14A C15A 0.7(3) . . . . ?
N13A C14A C15A C16A 0.2(3) . . . . ?
C12A N11A C16A N17A -179.63(19) . . . . ?
C12A N11A C16A C15A 0.0(3) . . . . ?
C14A C15A C16A N17A 179.1(2) . . . . ?
C14A C15A C16A N11A -0.5(3) . . . . ?
C16B N11B C12B O18B 178.27(19) . . . . ?
C16B N11B C12B N13B -0.7(3) . . . . ?
O18B C12B N13B C14B -178.4(2) . . . . ?
N11B C12B N13B C14B 0.6(3) . . . . ?
C12B N13B C14B C15B -0.1(3) . . . . ?
N13B C14B C15B C16B -0.3(3) . . . . ?
C12B N11B C16B N17B -179.75(18) . . . . ?
C12B N11B C16B C15B 0.3(3) . . . . ?
C14B C15B C16B N17B -179.7(2) . . . . ?
C14B C15B C16B N11B 0.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O10 H10 O9 0.95(4) 1.73(4) 2.603(3) 152(3) .
O19 H19B O13 0.87(3) 2.00(3) 2.834(3) 161(3) .
N13A H13A O18B 0.86(3) 1.97(3) 2.821(2) 174(2) .
N13B H13B O18A 0.83(3) 1.98(3) 2.813(3) 176(2) .
O8 H8 O11 0.97(3) 1.64(4) 2.585(2) 164(3) 1_545
O19 H19A O11 0.87(3) 2.16(3) 2.819(3) 132(3) 1_455
O19 H19A O9 0.87(3) 2.43(3) 3.096(2) 134(3) 2
N17A H17A O18B 0.88 1.91 2.785(2) 174.6 1_565
N17B H17C O18A 0.88 2.01 2.885(2) 175.0 1_545
N11A H11A N11B 0.90(3) 1.94(3) 2.836(3) 178(2) 1_565
N17A H17B O19 0.88 2.10 2.908(3) 152.0 2_466
N17B H17D O13 0.88 2.05 2.879(2) 156.7 1_545

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        28.54
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.079
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 30:70 ethanol/water'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_7
_database_code_depnum_ccdc_archive 'CCDC 1451661'
_audit_update_record             
;
2016-08-13 deposited with the CCDC.
2016-09-01 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'Fluorocytosinium sulfosalicylate fluorocytosine'
_chemical_name_common            '[FCYT+][SAA-][FCYT]'
_chemical_melting_point          527-532
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H14 F2 N6 O8 S'
_chemical_formula_weight         476.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9579(14)
_cell_length_b                   9.6421(19)
_cell_length_c                   14.749(3)
_cell_angle_alpha                101.51(3)
_cell_angle_beta                 101.98(3)
_cell_angle_gamma                98.62(3)
_cell_volume                     929.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3613
_cell_measurement_theta_min      1.45
_cell_measurement_theta_max      28.36

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9600
_exptl_absorpt_correction_T_max  0.9898
_exptl_absorpt_process_details   'SADABS, Bruker 2001'


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker DUO APEX II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11020
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         28.36
_reflns_number_total             4635
_reflns_number_gt                3613
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker DUO APEX II'
_computing_cell_refinement       Saint-Plus
_computing_data_reduction        Saint-Plus
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    X-Seed
_computing_publication_material  X-Seed

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0520P)²+0.1653P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4635
_refine_ls_number_parameters     326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1048
_refine_ls_wR_factor_gt          0.0952
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.032
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.22993(6) -0.18842(4) 0.22711(3) 0.01895(11) Uani 1 1 d . . .
C1 C 0.2641(2) 0.23831(18) 0.26019(12) 0.0187(3) Uani 1 1 d . . .
C2 C 0.2623(2) 0.10052(18) 0.27538(11) 0.0189(3) Uani 1 1 d . . .
H2 H 0.2664 0.0860 0.3375 0.023 Uiso 1 1 calc R . .
C3 C 0.2547(2) -0.01588(18) 0.20179(12) 0.0191(3) Uani 1 1 d . . .
C4 C 0.2553(3) 0.0065(2) 0.11119(12) 0.0255(4) Uani 1 1 d . . .
H4 H 0.2519 -0.0726 0.0604 0.031 Uiso 1 1 calc R . .
C5 C 0.2610(3) 0.1427(2) 0.09515(12) 0.0274(4) Uani 1 1 d . . .
H5 H 0.2649 0.1574 0.0337 0.033 Uiso 1 1 calc R . .
C6 C 0.2610(3) 0.25911(18) 0.16829(12) 0.0208(3) Uani 1 1 d . . .
C7 C 0.2590(3) 0.35950(18) 0.33817(12) 0.0206(3) Uani 1 1 d . . .
O8 O 0.2690(2) 0.32593(14) 0.42056(9) 0.0280(3) Uani 1 1 d . . .
H8 H 0.274(3) 0.408(3) 0.4687(17) 0.047(7) Uiso 1 1 d . . .
O9 O 0.2444(2) 0.48026(13) 0.32572(9) 0.0267(3) Uani 1 1 d . . .
O10 O 0.2566(2) 0.38932(14) 0.14727(9) 0.0271(3) Uani 1 1 d . . .
H10 H 0.260(4) 0.450(3) 0.1959(18) 0.048(7) Uiso 1 1 d . . .
H13B H 0.249(4) 0.650(3) 0.4327(18) 0.051(7) Uiso 1 1 d . . .
H17C H 0.181(4) 1.036(3) 0.7396(17) 0.045(7) Uiso 1 1 d . . .
H13A H 0.223(4) 0.666(3) 1.0156(19) 0.060(8) Uiso 1 1 d . . .
H11A H 0.247(3) 0.635(3) 0.7541(17) 0.042(6) Uiso 1 1 d . . .
O11 O 0.05652(18) -0.20170(13) 0.26745(8) 0.0244(3) Uani 1 1 d . . .
O12 O 0.4136(2) -0.18541(14) 0.29672(9) 0.0284(3) Uani 1 1 d . . .
O13 O 0.2016(2) -0.29373(13) 0.13733(9) 0.0294(3) Uani 1 1 d . . .
F1A F 0.34401(16) 0.26373(11) 0.86680(7) 0.0271(2) Uani 1 1 d . . .
N11A N 0.2507(2) 0.58796(16) 0.79898(10) 0.0203(3) Uani 1 1 d . . .
C12A C 0.2221(3) 0.67203(19) 0.88113(12) 0.0208(3) Uani 1 1 d . . .
N13A N 0.2264(2) 0.60614(16) 0.95514(10) 0.0237(3) Uani 1 1 d . . .
C14A C 0.2643(3) 0.47103(19) 0.95100(12) 0.0219(4) Uani 1 1 d . . .
H14A H 0.2633 0.4293 1.0041 0.026 Uiso 1 1 calc R . .
C15A C 0.3029(3) 0.39665(18) 0.87227(12) 0.0205(3) Uani 1 1 d . . .
C16A C 0.2978(2) 0.45525(18) 0.79092(11) 0.0182(3) Uani 1 1 d . . .
N17A N 0.3364(2) 0.38933(17) 0.71263(10) 0.0216(3) Uani 1 1 d . . .
H17A H 0.324(3) 0.434(2) 0.6653(15) 0.028(5) Uiso 1 1 d . . .
H17B H 0.392(3) 0.315(3) 0.7121(16) 0.038(6) Uiso 1 1 d . . .
H17D H 0.205(3) 0.910(2) 0.7873(17) 0.040(6) Uiso 1 1 d . . .
O18A O 0.1962(2) 0.79536(13) 0.88573(9) 0.0276(3) Uani 1 1 d . . .
F1B F 0.18612(17) 1.06780(11) 0.57864(7) 0.0302(3) Uani 1 1 d . . .
N11B N 0.2356(2) 0.73596(15) 0.64903(10) 0.0211(3) Uani 1 1 d . . .
C12B C 0.2465(3) 0.65228(19) 0.56592(12) 0.0221(4) Uani 1 1 d . . .
N13B N 0.2387(3) 0.70753(17) 0.48739(11) 0.0260(3) Uani 1 1 d . . .
C14B C 0.2193(3) 0.8465(2) 0.49009(13) 0.0261(4) Uani 1 1 d . . .
H14B H 0.2124 0.8832 0.4345 0.031 Uiso 1 1 calc R . .
C15B C 0.2102(3) 0.93038(18) 0.57214(12) 0.0222(4) Uani 1 1 d . . .
C16B C 0.2165(2) 0.87382(18) 0.65452(12) 0.0191(3) Uani 1 1 d . . .
N17B N 0.2022(2) 0.95325(18) 0.73557(11) 0.0245(3) Uani 1 1 d . . .
O18B O 0.2638(2) 0.52271(14) 0.56040(9) 0.0307(3) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O11 1.4520(13) . ?
S1 O13 1.4554(13) . ?
S1 O12 1.4560(14) . ?
S1 C3 1.7679(17) . ?
C1 C2 1.389(2) . ?
C1 C6 1.406(2) . ?
C1 C7 1.477(2) . ?
C2 C3 1.383(2) . ?
C3 C4 1.396(2) . ?
C4 C5 1.376(2) . ?
C5 C6 1.393(2) . ?
C6 O10 1.355(2) . ?
C7 O9 1.230(2) . ?
C7 O8 1.310(2) . ?
F1A C15A 1.3450(19) . ?
N11A C16A 1.356(2) . ?
N11A C12A 1.386(2) . ?
C12A O18A 1.220(2) . ?
C12A N13A 1.366(2) . ?
N13A C14A 1.360(2) . ?
C14A C15A 1.338(2) . ?
C15A C16A 1.421(2) . ?
C16A N17A 1.302(2) . ?
F1B C15B 1.3475(19) . ?
N11B C16B 1.344(2) . ?
N11B C12B 1.350(2) . ?
C12B O18B 1.261(2) . ?
C12B N13B 1.363(2) . ?
N13B C14B 1.360(2) . ?
C14B C15B 1.334(2) . ?
C15B C16B 1.423(2) . ?
C16B N17B 1.316(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S1 O13 113.08(8) . . ?
O11 S1 O12 111.73(8) . . ?
O13 S1 O12 113.24(8) . . ?
O11 S1 C3 104.92(8) . . ?
O13 S1 C3 107.12(8) . . ?
O12 S1 C3 106.03(8) . . ?
C2 C1 C6 118.93(15) . . ?
C2 C1 C7 120.51(15) . . ?
C6 C1 C7 120.49(15) . . ?
C3 C2 C1 121.29(15) . . ?
C2 C3 C4 119.26(16) . . ?
C2 C3 S1 117.19(13) . . ?
C4 C3 S1 123.44(13) . . ?
C5 C4 C3 120.29(16) . . ?
C4 C5 C6 120.52(16) . . ?
O10 C6 C5 118.00(15) . . ?
O10 C6 C1 122.37(15) . . ?
C5 C6 C1 119.63(15) . . ?
O9 C7 O8 123.54(15) . . ?
O9 C7 C1 122.47(15) . . ?
O8 C7 C1 113.98(15) . . ?
C16A N11A C12A 125.17(15) . . ?
O18A C12A N13A 123.47(15) . . ?
O18A C12A N11A 121.73(15) . . ?
N13A C12A N11A 114.80(15) . . ?
C14A N13A C12A 123.19(15) . . ?
C15A C14A N13A 120.14(16) . . ?
C14A C15A F1A 121.37(15) . . ?
C14A C15A C16A 120.65(16) . . ?
F1A C15A C16A 117.96(14) . . ?
N17A C16A N11A 120.49(16) . . ?
N17A C16A C15A 123.70(16) . . ?
N11A C16A C15A 115.81(15) . . ?
C16B N11B C12B 120.12(14) . . ?
O18B C12B N11B 120.30(15) . . ?
O18B C12B N13B 119.63(15) . . ?
N11B C12B N13B 120.06(16) . . ?
C14B N13B C12B 121.57(15) . . ?
C15B C14B N13B 118.78(16) . . ?
C14B C15B F1B 121.49(15) . . ?
C14B C15B C16B 120.28(16) . . ?
F1B C15B C16B 118.16(15) . . ?
N17B C16B N11B 119.40(16) . . ?
N17B C16B C15B 121.41(16) . . ?
N11B C16B C15B 119.18(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.9(2) . . . . ?
C7 C1 C2 C3 176.04(16) . . . . ?
C1 C2 C3 C4 2.1(3) . . . . ?
C1 C2 C3 S1 -174.34(13) . . . . ?
O11 S1 C3 C2 53.01(15) . . . . ?
O13 S1 C3 C2 173.44(13) . . . . ?
O12 S1 C3 C2 -65.36(15) . . . . ?
O11 S1 C3 C4 -123.25(16) . . . . ?
O13 S1 C3 C4 -2.82(18) . . . . ?
O12 S1 C3 C4 118.38(16) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
S1 C3 C4 C5 175.40(14) . . . . ?
C3 C4 C5 C6 -1.6(3) . . . . ?
C4 C5 C6 O10 -176.78(17) . . . . ?
C4 C5 C6 C1 2.8(3) . . . . ?
C2 C1 C6 O10 178.04(15) . . . . ?
C7 C1 C6 O10 1.1(3) . . . . ?
C2 C1 C6 C5 -1.5(3) . . . . ?
C7 C1 C6 C5 -178.46(16) . . . . ?
C2 C1 C7 O9 -174.10(16) . . . . ?
C6 C1 C7 O9 2.8(3) . . . . ?
C2 C1 C7 O8 5.1(2) . . . . ?
C6 C1 C7 O8 -177.97(16) . . . . ?
C16A N11A C12A O18A 173.89(16) . . . . ?
C16A N11A C12A N13A -5.8(2) . . . . ?
O18A C12A N13A C14A -176.95(17) . . . . ?
N11A C12A N13A C14A 2.8(2) . . . . ?
C12A N13A C14A C15A 1.1(3) . . . . ?
N13A C14A C15A F1A 178.94(15) . . . . ?
N13A C14A C15A C16A -2.3(3) . . . . ?
C12A N11A C16A N17A -174.80(16) . . . . ?
C12A N11A C16A C15A 4.7(2) . . . . ?
C14A C15A C16A N17A 179.10(17) . . . . ?
F1A C15A C16A N17A -2.1(3) . . . . ?
C14A C15A C16A N11A -0.4(2) . . . . ?
F1A C15A C16A N11A 178.37(14) . . . . ?
C16B N11B C12B O18B -179.77(16) . . . . ?
C16B N11B C12B N13B 0.2(3) . . . . ?
O18B C12B N13B C14B 179.75(17) . . . . ?
N11B C12B N13B C14B -0.2(3) . . . . ?
C12B N13B C14B C15B 0.8(3) . . . . ?
N13B C14B C15B F1B -178.34(15) . . . . ?
N13B C14B C15B C16B -1.3(3) . . . . ?
C12B N11B C16B N17B 178.72(16) . . . . ?
C12B N11B C16B C15B -0.7(2) . . . . ?
C14B C15B C16B N17B -178.10(18) . . . . ?
F1B C15B C16B N17B -1.0(3) . . . . ?
C14B C15B C16B N11B 1.3(3) . . . . ?
F1B C15B C16B N11B 178.42(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        28.36
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.059
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 30:70 methanol/water'
